Dimethyl Sulfoxide → N-[2-Nitro-4-fluoro-5-(methylpiperazin-1-yl)phenyl]acetamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethyl Sulfoxide	HCID 679	—
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	1-Methylpiperazine	HCID 53167	—
Reactant	Potassium Bromide	HCID 253877	—
Reactant	N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide	HCID 2773811	—
Product	N-[2-Nitro-4-fluoro-5-(methylpiperazin-1-yl)phenyl]acetamide	HCID 18792798	80%

Reaction Steps

N-[2-Nitro-4-fluoro-5-(methylpiperazin-1-yl)phenyl]acetamide (25.0 g, 80%) was prepared by an analogous procedure as described in preparation 1 (step 3) using N-(2-nitro-4-fluoro-5-chlorophenyl)acetamide (25.0 g, 0.107 mol) (obtained in preparation 1, step 2), 4-methylpiperazine (53.5 g, 0.535 mol), potassium hydroxide (9.05 g, 0.16 mol) and dimethyl sulfoxide (100 mL). mp 90-91° C.; IR (KBr) 3339, 1707, 1582 cm-1 ; 1H NMR (CDCl3) δ 2.24 (s, 3H, CH3), 2.32 (s, 3H, CH3), 2.56 (t, J=5.0 Hz, 4H, N(CH2)2), 3.42 (t, J=5.0 Hz, 4H, N(CH2)2), 7.90 (d, J=14.1 Hz, 1H), 8.36 (d, J=8.4 Hz, 1H), 10.70 (brs, 1H, NH); Mass (m/z) 296 (M+.).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06051570
Source dataset	uspto-grants-2000_04
ORD ID	ord-e73b184e09a54752a572a248c7e4e589
Source note	uspto-grants-2000_04